Metergoline

Metergoline (INNTooltip INN, BANTooltip British Approved Name), also known as methergoline and sold under the brand names Contralac (veterinary) and Liserdol (clinical), is a monoaminergic medication of the ergoline group which is used as a prolactin inhibitor in the treatment of hyperprolactinemia (high prolactin levels) and to suppress lactation.^[1][2][3]

Metergoline

Clinical data
Trade names	Contralac, Liserdol
Other names	Methergoline; FI-6337; [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester
Routes of administration	Oral
ATC code	G02CB05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name benzyl N-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methyl]carbamate
CAS Number	17692-51-2 N
PubChem CID	28693
IUPHAR/BPS	133
ChemSpider	26687 Y
UNII	1501393LY5
ChEBI	CHEBI:64216
ChEMBL	ChEMBL19215 Y
CompTox Dashboard (EPA)	DTXSID5042584
ECHA InfoCard	100.037.881
Chemical and physical data
Formula	C25H29N3O2
Molar mass	403.526 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OCc1ccccc1)NC[C@@H]3C[C@@H]4c5cccc2c5c(cn2C)C[C@H]4N(C3)C
InChI InChI=1S/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/t18-,21+,23+/m0/s1 Y Key:WZHJKEUHNJHDLS-QTGUNEKASA-N Y
NY (what is this?)  (verify)

Pharmacology

Pharmacodynamics

Metergoline is a ligand of various serotonin and dopamine receptors.^{[4][5][6][7][8][9]}

Activities of metergoline at various sites^{[4][5][10][11][12][8]}

Site	Affinity (Ki [nM])	Efficacy (Emax [%])	Action
5-HT1A	4.3	?	Antagonist
5-HT1B	5.2–36	?	Partial agonist
5-HT1D	0.60–11.7	?	Partial agonist
5-HT1E	776–1,122	?	?
5-HT1F	339–341	?	?
5-HT2A	0.12–2.3	?	Antagonist
5-HT2B	0.71–1.8	?	Antagonist
5-HT2C	0.18–1.8	?	Antagonist
5-HT3	>5,000–7,400	?	?
5-HT4	354	?	?
5-HT5A	630	?	?
5-HT5B	1,000	?	?
5-HT6	61–400	?	?
5-HT7	6.4–6.5	?	Antagonist
D2	?	?	Agonist
Notes: All sites are human except 5-HT3 (rat/pig), 5-HT4 (pig), and 5-HT5B (rat—no human counterpart).[4]